Monoazo dyestuff



acids and Patented June 2, 1925 UNITED STATES PA IEN OFFICE."

KARL THIESS, 0F LINDLINGEN,

' MONOAZO No Drawing.

To all whom it may concern: Be it known that I, KARL THIEss, a citizenof Germany, residing at Lindlingen, near Hoechst on-Main ,.Germany, havein vented certain new and useful Improvements in Monoazo Dyestuffs, ofWhich, the following is a specification. v .In U. S. patent application,Ser. No. 667,409filed Oct. 8, 1923, I haveset forth that by the actionof .diazotized m-aminobenzaldehyde and its substitution products andcompounds capable of splittin ,off m-aminoben zaldehyde upon pyrazo onesvaluable, fast yellow acid wool dyestuffs are obtained. I I havefurthermore found that' by coupling the above-mentioned diazo compoundswith acidylamino-alkylaminoand arylamino-naphtholmono and poly-sulfonicwool dyestuffs are obtained. The new dyestuffs dye wool yellow-red, red,bluish-red, violet brown to brown fast tints evenly and possess besidesa very great fastness to light and alkali and a surprisingly-greatfastness to washing and water. These dyestuffs which possess goodequalizingproperties are very suitable for dyeings on the animal fibrein an acid bath and for printings' on wool.

The dyestuffs arerepresented by the fol-4 lowing general formula:

' H CHO-R-N=N-R'N p in which R stands for a benzene residue which may besubstituted,- Rf stands for a residue of one of the naphtholrnono-- andpoly-su-lfon-ic acids, and X may be one of the residues, acidyl, aryland alkyl. "The dyestufls form differently colored powders with theirderivatives, new acid oEcfisT-oN-mlxm, GERMANY, assxenon TO mmawnnxnvonm. mnrs'rnn moms MANY, A CORPORATION or enamx;

80 BRUNING, 0F HOECHST-ON-MAIN, GER- mras'rtrrza.

hpplicationfiled 0ctobe'r 8, 1923. se al No. 667,410.

.soluble in hot water andin concentrated sulfuric acid with acharacteristic coloration and exhibit reactions characteristic of thealdehyde roup.

The fol owing examples illustrate my invention:

(1) 12, 1 kg. of m-ami-nobenzaldehyde are 'diazotized in the knownmannerand con led as usual withfa soda-alkaline solution 0 31, 5 kg.2-phenylamino-8-na hthol 6-sul-fonic acid. The dyestufl Whiciiis saltedout equalizes well and dyes wool in an acid bath vivid reddish-brownfast. tints. It is also Well. fit for .wool printing. The dyestuif hasprobably the formula:

' (2) The substitution of the 2-phenylamino-8-naphthol-6sulfonic acid by33 kg.

yields a dyestufi which gives a tint of a somewhat more reddish hue. v

'(3) If in'Example (1) the m-a'minobenzaldehyde is replaced b .15, 4 .kof 4-chloro-5-aminobenzaldehyde, t h e y e stuffs obtained give fastdark-brown tints.

pleted by a one hours stirring and the dyestuff thus obtained isisolated by salting out. It dyes wool in an acid bath pure red tintsred'tints.

of a blue hue of ayery good fastness to washing and fulling and of anexcellent fastness to light.

Th 1-H 1d d tflZ'-.

e benzoy agld yle S a yes u glv may be, used as well its substitutionproducts ing somewhat bluer tints.

(6) The replacing of the l-acetylamino- 8-naphtliol-3.6-disulfonic acidby the 1- acetylamino-8-naphthol 4-6rdisulfonic acid leadsto an equallyfast dyestulf giving pure (7) If in Example the acetyl-H-acid isreplaced by the 2-acetylamino-5-naphthol-7 sulfonicacid, a dyestuff isobtained which gives on wool in an acid bath yellow red tints of a goodfastness to water. washing, fulling and alkali. The fastness to light isparticularly good.

' .'(8) If one works according to Example (1) and replaces the2-phenylamino 8-naphthcl-G-sulfonic acid by 26.7 kg of2-ethylamino-8-naphthol6-sulfonic acid a dyestuif is obtained dyeing inan acid bath fast dark orange-brown tints.

If in Example (5) the acetyl-H-acid is replaced by. the correspondingmolecular quantity ,by weight of the 1-ethylamino-8-naphthol-3.5-disulfonic acid a dyestufl is obtained which dyes fast darkred tints.

. amino-5-naphthol- (10) .121 parts by weight of m-aminobenzaldehyde arediazotized as usual and combined with a soda alkaline solution of 400parts bywei ht of p-aminobenzoyl-2- %-sulfonic acid (90 per.

cent) at a temperature of 0'.5';'-Q'The formation of the dyestufli' atonce sets in and is completed by a short stirring. The dyestuff whichpartly is still dissolved be .salted out by common salt. It dyes wool inan acid bath clear yellow red tints of an excellent fastness to washing,fulling and to water. By an after-treatment with potassium chromate"there is obtaineda fast I claim is:

formula used as well the corresponding methylaminoandpropylaminonaphtholsulfonic acids.

- Having now described my .invention rwhat As new articles ofmanufacture, monoazo dyestuffs obtainable by'coupling the diazocompounds of m-aminobenzaldehyde and its substitution products and comounds capable of splitting as. m-amino enzaldehyde with theamino-naphthohmonoand poly sulfonic acids 'imwhichI one hydrogen oftheamino group may. ;be-replaced by one of the residues, alkyl, a-ryl'andacidyl, said dyestuffs having the-general formula E I H CHO R- N=N--R-NI in which It stands for a benzene residue which may be substituted, Rstands for a residue of one ofthje-naphthol monoand poly-sulfonic acidsand X may be one of the residues acidyl, aryl and .alkyl, said dyehotwater and in concentrated sulfuric acid .With a characteristiccoloration and exhibitin the reaction characteristics of the aldehydegroup.

In testimony whereof, I a'lfix my signature.

' KARL THIESS.

Witnesses: I

M. W. ALTAFFER, C. C. L. B. WYLES.

Certificate of Correction.

It is hereby certified that in Letters Patent No. 1,5-l0,665, grantedJune 2,. 1925,

upon the application of Karl Thiess, of Lindlingen, nearHoechst-on-Main, Germany, for an improvement in Monoazo Dyestuffs, anerror appears in the printed specification requiring correction asfollows: Page 2, strike out lines 59 to 7 3, comprising the formula, andinsert the following as the formula:

II HG and that the said Letters Patent should be read with thiscorrection therein that the same may conform to the record of the casein the Patent Office.

Signed and sealed thisf'Zth day of July, A. D. 1925.

[SEAL] WM. A. KINNAN,

Acting Commissioner of Patents,

